Iodoethane → HCID 57941617, compound

HRID 1437587Notes

Reaction equation

HRID 1437587 reaction equation
[N+:1]([O:4][CH:5]([CH2:35][O:36][N+:37]([O-:39])=[O:38])[CH2:6][CH2:7][CH2:8][O:9][C:10]([O:12][CH2:13]/[C:14](/[C:25]1[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][CH:26]=1)=[C:15](/[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)\[C:16]([OH:18])=[O:17])=[O:11])([O-:3])=[O:2].[CH2:40](I)[CH3:41].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N+:1]([O:4][CH:5]([CH2:35][O:36][N+:37]([O-:39])=[O:38])[CH2:6][CH2:7][CH2:8][O:9][C:10]([O:12][CH2:13]/[C:14](/[C:25]1[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:32])=[O:33])=[CH:27][CH:26]=1)=[C:15](/[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)\[C:16]([O:18][CH2:40][CH3:41])=[O:17])=[O:11])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 11753385HCID 11753385, compound

Product 1

HCID 57941617HCID 57941617, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.6 g (2Z)-4-[({[4,5-bis(nitrooxy)pentyl]oxy}carbonyl)oxy]-3-[4-(methylsulfonyl)phenyl]-2-phenylbut-2-enoic acid in 20 mL of DMF at RT was added 3 mL of ethyl iodide and 485 mg of potassium carbonate under nitrogen. The reaction was stirred for 30 min, and then quenched by addition of NH4Cl sat., extracted with EtOAc, washed with water (3×), brine and dried over sodium sulfate. Purification by flash chromatography afforded 1.42 g of the titled compound as a colorless oil. 1H NMR (acetone-d6, 500 MHz): δ 7.78 (d, 2H), 7.45 (d, 2H), 7.17 (t, 3H), 7.09 (d, 2H), 5.52 (d, 1H), 5.26 (s, 2H), 5.00 (dd, 1H), 4.73 (dd, 1H), 4.28 (q, 2H), 4.16-4.12 (m, 2H), 3.06 (s, 3H), 1.88-1.79 (m, 4H), 1.27 (t, 3H).

Workup

  1. customquenched by addition of NH4Cl sat.
  2. extractionextracted with EtOAc
  3. washwashed with water (3×), brine
  4. dry with materialdried over sodium sulfate
  5. customPurification by flash chromatography

Sources & evidence

ORD record
ord-104742f367704c4e9b749403a0d59913
Source dataset
uspto-grants-2009_11
Patent number
US07622501B2

Reaction notes

Loading…